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I’m looking for Leonard. There’s a good chance he might be here, lurking in his favourite haunt, but I can’t see a thing; it’s sheeting with rain, the kind of Montreal rain that seeps into the sidewalk then steams up onto windows and into trees, reducing views of the forested mountain after which the city is named — usually crisply framed at the end of side streets — to a blurry pointillist landscape. Mount Royal looms above the city — at this time of year, a sharp, fiery peak of poster-paint-bright reds, oranges and yellows, although all I can see on the horizon is rusty mist.

I’m standing outside the Main Deli Steak House on The Main (officially Saint Laurent Boulevard), one of Montreal’s major thoroughfares. My attempts to ascertain whether Mr Cohen is inside are rendered impossible by the humidity-fogged windows. Seeking out arguably the city’s most famous son at this spot has been something of a preoccupation on trips here ever since a Montrealer friend told me this tantalising fact about the singer-songwriter’s dining habits on my first visit in the 1990s. (Sadly, I wasn’t to know that this trip represented my last chance.)

Born in the comfy, middle-class district of Westmount, Cohen later decamped to a more fittingly boho apartment nearby, on The Main. Here, in this former working-class Portuguese ’hood, in bars and diners such as the Main Deli Steak House, Leonard could, according to Canadian music journalist David Sax, “watch the gangsters, pimps and wrestlers dance around the night”.

In the ’60s, seeking his musical fortune, he hopped across the border to New York, then onwards to LA, but the Steak House remained a frequently returned-to hangout. “He was in there pretty much every time I was,” David had shrugged. “At 3am, after clubbing, we’d find him smoking cigarettes and drinking with his friends.” This revelation felt thrillingly egalitarian, somehow signifying a city that truly embraced its arts and artists. Even in the ’90s, Cohen’s former hippy enclave, the Plateau (centred around The Main) was still thick with artful, outsider industry.

Here, where Montreal’s distinctive wrought-iron staircases spiral up the facades of Victorian houses, several artists’ collectives could still be found, set above thrift stores where army surplus gear was racked collar-to-cuff with acid smiley T-shirts and rainbow-coloured Kickers.

Back then, The Main’s Plateau and Mile End areas were home to laundromats that doubled as literary cafes and recording studios that morphed into clubs at select hours. As a 20-something seeking alternative R&R, I loved this street and it’s a love that’s endured; its versatile venues welcoming the young, the old and pretty much all walks of life. Running west from the docks through the city, this boulevard has traditionally been a place for outsiders. Its strip clubs and jazz bars drew Americans across the border during a Prohibition era that was largely ignored here in Quebec. These establishments gave Montreal — and The Main, in particular — something of a licentious heritage.

At Saint-Laurent’s easternmost end, one of these legendary red-light venues still stands: Café Cléopâtre, the so-called ‘Queen of The Main’. Today, its kitsch, Egyptian-exotica signage, advertising ‘Danseuses a gogo’ looks wildly incongruous flanked by abandoned warehouses and a construction site/car park. “There was a big clean-up for Expo 67,” explains my guide, Amelie Rolland. “Most of the dive bars and strip clubs were razed for parking lots — which later turned into spaces where most of Montreal’s outdoors music and arts festivals were born.” But Cléopâtre held firm, a beacon of burlesque. More recently, when the Queen of The Main faced bulldozers to make way for municipal offices, she was saved by petitions and sit-ins by her loyal retinue of patrons, partiers and drag queens.

Tempting though it is to lose a few layers of soggy clothing, it’s too early for striptease, so Amelie and I turn our backs on Cléo’s and head across the road to the Montreal Pool Room to sample another city staple. Pool is no longer played in this tatty, lino-floored landmark but they’re still serving up the poutine. Quebec’s famous working man’s dish of chips, cheese and gravy has lately been gentrified with foie gras and lobster at such gourmet city spots as Garde Manger and Au Pied de Cochon. But here it’s served just as it should be: piled high on a cardboard carton, steaming like a sidewalk in the rain.

Marché Jean-Talon covered market, Saint Laurent Boulevard

The great divide

For all its unifying, nocturnal energy, The Main is also Montreal’s original dividing line. Not only does the boulevard — one of the lesser-known national historical sites — bisect the Island of Montreal from the Prairies River down to the St Lawrence River, it also traditionally divided the city’s original Francophone residents from later Anglophones. It’s a social division that can be seen across the province, led largely by a Francophone separatist movement that’s spawned two knife-edge referendums. “Each time we voted ‘no’ to Quebec separating from Canada, but the movement for independence will likely never go away,” says Amelie. “I have French heritage but I’m not a separatist. I’m not against it as a concept but I’ve never seen the benefit. I’ve never heard a compelling reason or convincing economic plan; a bit like your Brexit, no?”

Quebec’s most recent vote, in 1995, produced a photo finish 50-49% win for Federalists. But the reign of the PQ (Partie Québécoise) during that decade saw Anglophone and international investment flee the province for Toronto. The subsequent economic slump hit Montreal hard. During my visits in the ’90s, seemingly every shop front and condo was plastered with signs that read ‘à louer’ (for rent). But this landscape of cheap rent, squats and free studio space — plus a longstanding government commitment to providing grants, funding and tax breaks for artists, saw a generation of creative Montrealers bloom.

Montreal musicians, for one, became an international marker for creative innovation, with artists such as David Bowie frequently border-hopping from his home in New York to plunder local recording studios for inspiration. Arcade Fire, The Dears, Grimes and Godspeed You! Black Emperor are among the seemingly never-ending crop of local bands that have lately dominated the world stage. Indie thrives and so too does electro, with Montreal now a must-do extension to the New York-London-Ibiza tours of big-name DJs. The city also finds itself at the epicentre of Canadian job creation, led in part by a thriving tech and multimedia sector whose roots reach back to the pioneering start-up culture of the post-referendum ’90s.

“Most of them can’t afford to live in the Plateau any longer,” says Anne-Marie Pellerin, my guide through the blossoming Mile-Ex neighbourhood, just to the west. “So this is where many artists and architects have migrated. Montreal is a creative city — mostly because you can still make the things you’re passionate about without being too scared about paying the rent.” Anne-Marie’s tour outfit, Spade & Palacio takes visitors beyond the Plateau, to explore Mile-Ex’s coffee houses, street art and incredible ethnic eats. “We don’t visit the big art galleries or do tastings of bagels, smoked meat or poutine. People can find these classics themselves.”

Today, The Main and Mile-Ex represent something far more cosmopolitan than a French-English frontline. And while the waves of Chinese, Italian, Spanish, Latino, African and Southeast Asian settlers who came here may have moved on from their original postcodes, landmark restaurants still act as cultural markers of former ethnic neighbourhoods. Although perhaps only in Montreal will you find a restaurant in the Little Vietnam area offering menus in Vietnamese, Spanish, English and French. At landmark Salvadorian restaurant Los Planes, we snack on horchata and pupusa (stuffed tortillas), then walk off the excess admiring the hundreds of murals that adorn the walls along The Main as it passes through Mile-Ex: a gallery of immigrant, LGBT and political statements.

Fuelled by a cold-press coffee from food-truck-turned-cafe of the moment Dispatch Coffee, we dig deeper into the backstreets. Free of the strict heritage laws designed to preserve the Plateau’s wrought-iron staircase-clad landscape, Mile-Ex is an architect’s blank canvas. “They can really start from scratch and build the house of their dreams,” says Anne-Marie, as we wander past modern loft apartments, ’50s bungalows, boxy ’60s duplexes and auto repair shops. And then — ping! — up pops a vision of mid-century California or modern-day Scandinavia, all picture windows and polished cement. It’s a refreshingly bold North American vision, softened by the ruelles vertes (green alleyways) that back most blocks.

Originally allowing access for refuse trucks, these green alleys now act as community gardens, bolstered by forward-thinking city funding. I miss the chance to try out one of Mile-Ex’s most happening bars, Alexandraplatz Bar, as I walk right past this no-sign former warehouse unawares — all too transfixed by the lurid murals on surrounding walls. One of them depicts scandal-afflicted former prime minister Stephen Harper as a War of the Worlds-style machine, complete with laser-blasting eyes and a pet cat in his arms. I suppose when you’ve got the seemingly untouchable Justin Trudeau as PM, satirists have to look to the past for material.

Poutine, Saint Laurent Boulevard

Downtown funk

“We really have so many creative companies at our fingertips here in Montreal,” says Amahl Hazelton, of Montreal’s Moment Factory. This multimedia entertainment studio has brought its arty video, lighting and architectural vision to Broadway shows, massive stadium rock concerts and even the new LAX terminal, as part of America’s largest immersive multimedia airport art installation. But it’s very much a Montreal company, and one selected to help paint the town red, along with myriad other colours, for the city’s Big Birthday this year.

This May, Montreal reaches the grand old age of 375, making it one of the most geriatric of North America’s European-settled cities. Nonetheless, this habitually youthful metropolis is intensifying its already jam-packed programme of arts festivals, to celebrate its founding. This year, Canada also marks the 150th anniversary of becoming a country, so 2017 promises a pretty momentous knees-up. One highlight of the celebrations will be the lighting of the Jacques Cartier Bridge. “It was all but invisible at night,” says Amahl of the cantilevered 1920s construction that spans the Saint Lawrence River and adorns most city postcards. “So we’ve fitted its skeleton in LED lights that change according to the mood of the city.” Quite how this interactive illumination works is a complex bit of tech mystery, fed by data sources as diverse as social media, barometrics, traffic flow, and even the Montreal Canadiens hockey team’s standing in the Stanley Cup (if their current 20-year low is anything to go by, we’re looking at a deep, depressive blue).

For far less conspicuous birthday renovations, Amahl points me underground. Famed in the ’60s as a futuristic ‘underground city’, Montreal’s miles of concrete subway and subterranean shopping malls can be life-saving on -20C-averaging winter days, but as tourist attractions are something of a damp squib. But this is set to change.

Amahl and I are at Youville Pumping Station, a Scottish-brick building in Old Montreal, a landmark from the city’s industrial era, where visitors learn about the city’s turn-of-the-century plumbing. It’s technically an obscure annex to the city’s superb Pointe-à-Callière Museum (archaeology and history), which sits across the street on the spot where Montreal was founded in 1642 as an outpost of France — a riverside site where First Nations peoples had been gathering for centuries before.

The tunnels between Youville and the Pointe-à-Callière Museum have been renovated and augmented by Moment Factory’s storytelling projections, and when finished will lead visitors through strata of archaeological history. And it looks like it won’t stop there, with the next project being to unearth the site of unified Canada’s first parliament building from beneath a parking lot, a few blocks up. All I can see now, though, are big holes in the road; the bearded and blue-haired denizens of surrounding warehouse hotels and digital studios going about their business, oblivious.

I pop in for a rosemary-topped cocktail at the new Hotel William Gray, whose hipster aspirations are as far-reaching as its seriously wow-factor panoramic roof, overlooking port and city. A bartender recommends the nearby Björk Digital exhibition, complete with ground-breaking virtual-reality technology added especially for the Montreal leg of this show’s world tour. But it’s time-specific tickets only, so to kill time I wander down to the docks — where I finally find Leonard.

Part of the City’s 375th celebrations include the Cité Mémoire — a sound and light show in which a tableaux of events from Montreal’s history is projected onto buildings, trees and silos; the displays activated on demand by phones and tablets via a free app. As I pass, a sweeping projection of a barefoot girl curls and twirls up the side of the port’s clock tower, in front of which a crowd has gathered. I’m handed some headphones by a kindly fellow spectator and realise the girl is dancing to Cohen’s words:

Suzanne takes you down to her place near the river,
You can hear the boats go by, you can spend the night forever
And you know that she’s half-crazy but that’s why you want to be there

And we do.

Essentials

Getting there and around
Airlines offering nonstop flights from Heathrow to Montreal include Air Canada, Air Transat and British Airways.Average flight time: 7h 30m.
The city’s underground system, Montreal Metro, covers most of the city, with buses filling the gaps.

When to go
Year-round, although summer (arts festival season) is glorious, with the mercury regularly hitting the 30Cs.